Elon Musk, far and away the richest man on the planet, is pouring tens of millions of dollars into efforts to get Donald Trump elected. In addition to his massively valuable promotion of Trump’s messaging on X—an in-kind donation if ever there was one—he reportedly gave $50 million to a group linked to immigrant-hater Stephen Miller, the architect of Trump’s morally abominable family separation policy. And then there’s the legally problematic $100 payments and $1 million lottery-style giveaways he’s been offering registered swing-state voters who sign a petition stating the following:
The First and Second Amendments guarantee freedom of speech and the right to bear arms. By signing below, I am pledging my support for the First and Second Amendments.
Weird, right? But Musk’s return on investment could be huge if Trump prevails and gives him even more power over the very government at whose teat Musk’s companies were nurtured to profitability—and on which they continue to depend. Also, let’s remember, tens of millions for this dude is the equivalent of pocket change for the rest of us. Here’s how much of Musk’s net worth $50 million represents:
0.000183486238532
But what of his philanthropy, you ask? Didn’t Musk sign Bill Gates’ “Giving Pledge,” vowing to give at least half of his wealth to charity?
Yes, he signed up in 2012, for what it’s worth. But he’s running way behind on his giving. Consider that, in all of 2022, according to his foundation’s latest tax filing, he gave $160.5 million to charitable causes. Musk made more than that just yesterday—a great deal more.
Forbes Real Time Billionaires
That’s right, Musk’s net worth increased by $2.7 billion on Friday, according to Forbes’ Real-Time Billionaires, a database that serves as a reminder of just how far our supposedly egalitarian American experiment has devolved into plutocracy—or oligarchy, if you prefer—a situation that founder John Adams had hoped we would avoid (though he wasn’t terribly confident that we would).
Put another way, the amount Musk gave to charity in one year is this much of what he gained in a day:
0.05962962962963
Six percent!Musk, by the way, is now roughly 100 times as rich as he was when he signed the pledge—a scenario Andrew Carnegie would consider grotesque. He’d best start acting more like MacKenzie Scott. Because, as a trusted advisor to industrialist John D. Rockefeller once warned his boss:
You must distribute it faster than it grows! If you do not, it will crush you, and your children, and your children’s children!
Now, Musk did contribute almost $2.3 billion in Tesla stock to his foundation in 2022, earning a fat tax break and locking in a huge, tax-free capital gain at the expense of America’s taxpayers. But our rules governing philanthropy are so toothless that he need only disburse a small fraction of these “charitable” assets. His foundation’s nest egg—roughly $7.2 billion at the end of 2022—generated $309 million in investment income that year, and the value of its unsold assets gained at least $373 million. Yet the amount it gave to charity was about the same as the previous year.
Federal law requires private foundations to spend down 5 percent of their assets annually (which includesoverhead). Musk’s 2022 obligation was about $358 million—he didn’t give even half that. The government lets foundations average their disbursements over five years, but he’ll have to pick up his pace considerably.
Lest you were hoping the Musk Foundation’s tax documents would reveal sinister causes to which he may have donated, sorry to disappoint. His public giving is unobjectionable. What you have to watch out for, though, is the transfers to donor-advised funds. His foundation has, since 2018, moved more than $75 million over to a fund at Fidelity Charitable. For some unfathomable reason, the government lets such transfers count toward a foundation’s mandatory charitable payout.
Donor-advised funds are even more problematic than private foundations—although both cost taxpayers a fortune and are, as I explained in our must-read American Oligarchy issue, profoundly undemocratic. Not only are the creators not obligated to dole out a minimum of their assets each year, they are not obliged to reveal whom they are giving to. It’s dark money, in other words— convenient for anyone who wants to give secretly to odiousnonprofits, including groupswilling to subvert the democratic process if it will help put a certain candidate back in the White House.
Jimmy Carter turned 100 on October 1, making him the oldest former president. According to his family, Carter, also a former Georgia governor who has been in hospice care since February 2023, wanted to live long enough to cast his ballot for Kamala Harris. He passed that milestone on Tuesday, as early voting commenced in Georgia.
But with three weeks to go before Election Day, this raises a question? If Carter casts an absentee ballot and doesn’t make it until November 5, will the state count his vote?
Georgia law doesn’t address this question.
According to the National Conference of State Legislatures, most states haven’t stipulated what to do in such cases. Ten specifically mandate the counting of absentee ballots regardless of the voter’s corporeal status. (Connecticut allows it only when the deceased voter had been an active military member.) Another 10 states specifically forbid the counting of such ballots. Two—Kentucky and Mississippi—don’t have a statute addressing the issue, but reject the ballots based on legal opinions by their attorneys general. Three others allow residents to challenge such ballots. Here’s a map based on the NCSL tally:
Were I your king, or an authoritarian leader—something we may have soon enough—I would allow such votes because they reflect the hopes and fears of then-living Americans for their own near futures and for the futures of their families.
The reason we don't let people cast votes after death is obvious: They're dead, which means those votes would be fraudulent. (Besides, how far back would you go? Would you let the late Shirley Chisholm vote? How about Barry Goldwater?)
My preference on the absentee ballot question suggests I would be a benevolent authoritarian. But the one we might end up with would, I fear, only allow the votes of newly deceased Republicans to be counted.
Heck, he might even Make Goldwater Eligible Again. (MGEA?)
Jimmy Carter turned 100 on October 1, making him the oldest former president. According to his family, Carter, also a former Georgia governor, who has been in hospice care since February 2023, wanted to live long enough to cast his ballot for Kamala Harris. He passed that milestone on Tuesday, as early voting commenced in Georgia.
But with three weeks to go before Election Day, this raises a question? If Carter casts an absentee ballot and doesn’t make it until November 5, will the state count his vote?
Georgia law doesn’t address this question.
According to the National Conference of State Legislatures, most states haven’t stipulated what to do in such cases, which are not likely numerous enough to sway even a local election—unless, perhaps, it’s for a seat on a local nursing home’s resident advisory committee.
Ten states specifically mandate the counting of absentee ballots regardless of the voter’s corporeal status. (Connecticut allows it only when the deceased voter had been an active military member.) Another 10 states specifically forbid the counting of such ballots. Two—Kentucky and Mississippi—don’t have a statute addressing the issue, but reject the ballots based on legal opinions by their attorneys general. Three other states allows residents to challenge such ballots. Here’s a map:
Were I your king, or an authoritarian leader—something we may have soon enough—I would allow such votes because they reflect the hopes and fears of then-living Americans for their own near futures and for the futures of their families.
The reason we don't let people cast votes after death is obvious: They're dead, which means those votes would be fraudulent. (Besides, how far back would you go? Would you let the late Shirley Chisholm vote? How about Barry Goldwater?)
My preference on the absentee ballot question suggests I would be a benevolent authoritarian. But the one we might end up with would, I fear, only allow the votes of newly deceased Republicans to be counted.
Heck, he might even Make Goldwater Eligible Again. (MGEA?)
As Donald Trump campaigns to be a dictator for one day, he’s asking: “Are you better off now than you were when I was president?” Great question! To help answer it, our Trump Files series is delving into consequential events from the 45th president’s time in office that Americans might have forgotten—or wish they had.
President Donald Trump was lying profusely about his administration’s most notable achievement, the Tax Cuts and Jobs Act (TCJA), even as he sat down to sign the bill into law in 2017, a few days before Christmas.
“As you know, we had the largest tax cuts in our history just approved,” he remarked at the “rush-job” Oval Office signing ceremony, from which the usual gaggle of fawning Republican legislators was excluded—the souvenir pens were instead offered to the lucky few reporters on hand. “This is bigger than, actually, President Reagan’s.”
Uh, not even close—though it was the biggest corporate cut. Thanks to his tax bill, Trump went on, corporate America was already “making tremendous investments. That means jobs; it means a lot of things. And we’re very happy. So that’s AT&T, Boeing, Sinclair, Wells Fargo, Comcast, and now many other companies.”
The rich are feasting on America’s economic pie. Republican tax cuts have set them on a steep upward wealth trajectory, far and away from the “little people.”
The executives sure were happy. The legislation slashed corporate income taxes dramatically, from 35 percent to 21 percent. Not surprising, given that, according to the nonprofit Public Citizen, more than 7,000 lobbyists—on behalf of a who’s who of Corporate America—helped hammer out the bill’s details. That’s 13 lobbyists per lawmaker.
And what did these joyful companies do with their windfall? Build new factories? Hire more workers? Raise wages? Stimulate economic growth? There was some of that, sure. But the cuts came “nowhere close to paying for themselves,” the New York Times later reported, and have added more than $100 billion a year to the deficit.
Just about every Republican president since Reagan has relied on the same debunked theory to advance tax cuts for corporations and wealthy Americans. It’s called supply-side (or “trickle-down”) economics. The idea is that if we give rich folks more money, they’ll invest, build companies, and create good jobs. The economic benefits will then trickle down to what the late New York heiress Leona Helmsley—whom the press nicknamed “Queen of Mean”—allegedly called the “little people.” (That fun fact emerged during testimony at her 1989 trial for tax evasion—where she was found guilty. Helmsley died in 2007, famously leaving $12 million to Trouble, her pampered little dog, but nothing to two of her four grandchildren.)
Trump’s corporate cuts, predictably, trickled not down but up. As I wrote in my 2021 book, Jackpot, the first instinct of executives and board members after Congress passed the TCJA was to enrich themselves:
S&P 500 firms spent a record $806 billion in 2018 buying back their own shares on the public markets. The Harvard Business Review notes that senior executives, paid largely in stock and stock options, use buybacks to manipulate share prices “to their own benefit” and the benefit of “investment bankers and hedge-fund managers” who are further enriched “at the expense of employees, as well as continuing shareholders.”
Buybacks are indeed marvelous for executives and Wall Street bankers. By reducing the number of outstanding shares on the market, they drive up the stock price to the benefit of major shareholders. But they’re bad news for workers, who have traditionally benefitted from excess corporate profits and their reinvestment in operations and equipment, which tends to strengthen the business and bring new jobs. Buybacks also can be bad for long-term investors, because they encourage a short-term mindset in the C-suite and can be used to mask a firm’s underperformance.
Notably, every one of the firms Trump praised by name during the signing ceremony notched major buybacks soon afterward: Sinclair’s board greenlit $1 billion in the months to follow. Boeing’s board approved $19 billion, and numerous reports have blamed the company’s aircraft safety fiascos in part on its lust for buybacks. (Late last week, the company announced it would lay off roughly 17,000 people, or 10 percent of its workforce.)
On Trump’s watch, Congress doubled the gift and estate tax exemption. A rich couple can now leave their kids $27.2 million without paying one dime in tax.
AT&T repurchased $692 million worth of its stock in 2018 amid reports that it had been laying off workers and closing call centers—and completed nearly $2.5 billion in buybacks the following year. Wells Fargo was in for almost $41 billion, and Comcast shelled out $8.4 billion for buybacks and dividends (which it juiced by 10 percent).
“We give stock to corporate managers to convince them to create the kind of long-term value that benefits American companies and the workers and communities they serve,” Robert Jackson Jr., who then served on the Securities and Exchange Commission, declared in a June 2018 speech. “Instead, what we are seeing is that executives are using buybacks as a chance to cash out their compensation at investor expense.”
Even when wealthy businesspeople are incentivized to “create value,” results may vary. “A friend of mine, Bob Kraft, called me last night, and he said this tax bill is incredible,” Trump remarked at the signing.
“He owns the New England Patriots,” Trump said, “but he’s in the paper business too. And he said, based on this tax bill, he just wanted to let me know that he’s going to buy a big plant in the great state of North Carolina, and he’s going to build a tremendous paper mill there.”
I looked up that “tremendous” paper mill. Trump, as usual, botched the details. The plant is in Catawba,South Carolina. Kraft’s company, New-Indy, took it over in September 2018, after which it became a total nightmare for the community—generating more than 47,000 complaints of noxious odors “similar to rotten eggs, dirty diapers or other foul smells,” including from people in North Carolina.
The Institute for Taxation and Economic Policy released an analysis of whom Trump’s new tax proposals would benefit. Guess what: It probably isn’t you!
Another big deal, Trump said, were the estate tax changes in the tax bill: “Something very important to me,” he said (if you can imagine anyone not named Trump being important to Trump), were “the family farmers and small-business owners who lost their business because of the estate tax. Most of them won’t have any estate tax to pay. It will be a great thing for their families. You can leave your farm to your family. You could leave your business, your small business to your family—not even so small, because the numbers are pretty big here.”
They are big! The TCJA doubled the gift and estate tax exemption and pegged it to inflation, which means, as of 2024, a well-heeled couple can leave $27.2 million to their heirs without paying one dime in tax.
But that won’t save any “family farms.” That’s a well-worn Republican talking point that amounts, fittingly enough, to a heap of cow manure. Back in 2017, a researcher with the nonpartisan Center on Budget and Policy Priorities (CBPP) pointed out that only 50 small farms or businesses would be on the hook for federal estate tax that year (a “small” business can have up to $40 million in annual revenues and 1,500 employees), and most would likely have other assets, such as stock, that could be liquidated if need be to cover the tax. Existing law, she also pointed out, allows estates “to spread their payments over a 15-year period at low interest rates.” America’s farmers were never in danger.
The Reagan tax cuts enacted in 1981 and 1986 added up to biggest break for wealthy Americans since 1920. The top marginalrate owed in 1981 on the uppermost income tierof the nation’s highest earners—anything exceeding $215,400 for a couple (about $760,000 in today’s dollars)—was slashed dramatically, from 70 percent when Reagan took office to 28 percent the year he left. Congress also reduced the gift/estate tax, more than tripled the lifetime exemption—the amount parents can leave their offspring tax-free—and trimmed taxes on capital gains and corporate profits.
And what was the outcome of all this largesse? Another snippet from Jackpot:
In 2012, a researcher at the nonpartisan Congressional Research Service sought to determine whether the Reagan cuts and other reductions in marginal income tax rates over the prior sixty-five years had benefited the overall economy. He came up short. The tax cuts did not appear to be correlated with more robust saving, investment, or productivity growth. They did, however, appear to be associated with rich people making a lot more money than before. There was no evidence that the cuts expanded America’s economic pie, the report noted, “but there may be a relationship to how the economic pie is sliced.”
You might even say the very rich pigged out on the pie. The Reagan cuts set America’s most affluent citizens on a steep upward wealth trajectory, soaring them far and away from the “little people.”
This chart from Jackpot shows average household wealth over time for the richest 1 percent, richest 10 percent, and all Americans, in 2018 dollars.Carolyn Perot
Supply-side economic arguments would later enable George W. Bush to slash taxes further. Among other provisions, the 2001 and 2003 bills he signed reduced the top income tax rate, then 39.7 percent, to 35 percent—lower even than today—and began phasing out the estate tax, which Congress briefly repealed in 2010, only to reinstate it the following year.
“High-income taxpayers benefitted most from these tax cuts, with the top 1 percent of households receiving an average tax cut of over $570,000 between 2004-2012,” explains a CBPP analysis. By 2010, the report notes, the Bush cuts resulted in a 1 percent bump in annual after-tax income for the poorest fifth of US families, whereas the top-earning 1 percent enjoyed a 6.7 percent increase.
Unfair? Sure. But did the Bush cuts ever deliver the economic results supply-siders promised? Nope. “Evidence suggests that they did not improve economic growth or pay for themselves, but instead ballooned deficits and debt and contributed to a rise in income inequality,” notes the CBPP.
Fast forward to 2024, when Trump told a crowd of “rich as hell” donors he’ll give them more tax cuts if elected to a second term. They cheered! Joe Biden and Bernie Sanders made a Facebook video.
Trump has said he wants to cut the corporate income tax further, too—to 15 percent. (Kamala Harris proposes raising it to 28 percent, still well below the pre-Trump rate of 35 percent.) And he keeps introducing new, ill-conceived, tax proposals on the campaign trail—mostly regressive—adding to a haphazard plan that the nonpartisan Committee for a Responsible Federal Budget projects will cost the federal government, depending on economic conditions, anywhere from $1.5 trillion to $15.2 trillion over a decade. (The Harris plan, the group projects, would cost between zero and $8.1 trillion.)
On October 7, the nonpartisan Institute for Taxation and Economic Policy released an analysis of whom Trump’s tax proposals would benefit.
It’s probably not you.
ITEP
Love it or hate it, at least now you better understand the Republicans’ dirty little secret: Supply side economics, cutting taxes on the wealthy, doesn’t work. It has never worked. It’s complete bullshit. But alas, it’s the sort of bullshit that refuses to be composted.
Project 2025, the Heritage Foundation’s blueprint for a second Donald Trump presidency—you know, that document he knows nothing about even though 140 people from his first administration, including six former Cabinet members, helped create it—is full of delightful little Easter eggs. One provision that has attracted almost no public notice, perhaps because it seems so reasonable, is the authors’ call for the government to create “universal savings accounts” (USAs).
Heck, it even has a patriotic name!
All taxpayers should be allowed to contribute up to $15,000 (adjusted for inflation) of post-tax earnings into Universal Savings Accounts (USAs). The tax treatment of these accounts would be comparable to Roth IRAs. USAs should be highly flexible to allow Americans to save and invest as they see fit, including, for example, investments in a closely held business. Gains from investments in USAs would be non-taxable and could be withdrawn at any time for any purpose. This would allow the vast majority of American families to save and invest without facing a punitive double layer of taxation.
But let’s think about this. Over the past few decades, Congress passed a series of bills to help Americans save for old age privately via government-subsidized pensions, 401(k)-type plans, and individual retirement accounts—of which Roth IRAs are one type. These tax breaks and program expansions have all been bipartisan, and all have passed with flying colors, because they sound pretty good—much like these universal savings accounts—until you examine them more closely.
And then you have to ask: Good for whom?
Taken collectively, the various retirement subsidies are mind-bogglingly expensive. They are, in fact, the federal government’s single largest tax expenditure, projected to deprive the Treasury of almost $2.5 trillion over five years (2023–2027), according to the bipartisan Joint Committee on Taxation (JCT)—mostly, as I’ve written, to the wildly disproportionate benefit of our most affluent.
In the most extreme case reported thus far (by ProPublica), the Silicon Valley entrepreneur and political puppet-master Peter Thiel used a $1,700 contribution to his Roth IRA—Roths are intended for middle-class savers—decades ago to purchase 1.7 million “founder’s shares” of PayPal at one-tenth of a cent each. Because of that, by 2002, the year eBay purchased PayPal, ProPublica reported, the balance in Thiel’s Roth was up to $28.5 million, with all of those gains nontaxable. He then repeated this cycle with other fledgling companies, culminating in a Roth IRA containing north of $5 billion in assets.
Thiel was an outlier, but ProPublica identified others with IRAs worth tens or hundreds of millions of dollars. Indeed, in 2021, at the request of Senate Finance Committee chair Ron Wyden (D-Ore.), the JCT counted more than 28,000 taxpayers with traditional or Roth IRAs with balances exceeding $5 million—497 of the accounts contained $25 million or more.
What does this have to do with Project 2025? Well, USAs would be Roths on steroids. The $15,000 annual contribution limit is more than twice what people under 50 are allowed to contribute to a Roth. And even the highest earners could contribute to a USA—with Roths, you can only make the full contribution if your income is $146,000 or less. The fact that one needn’t wait until retirement to withdraw funds make USAs all the more compelling.
Heck, if you can afford to put $15,000 a year into an investment fund and let it take a tax-free ride—which the majority of Americans cannot—there would be no reason not to. “High bracket taxpayers would get the biggest tax benefits and could find the disposable savings to participate most easily,” says Steven Rosenthal, a senior fellow at the Tax Policy Center who has written about the retirement system’s income and race disparities.
Roth IRAs cost taxpayers relatively little, mainly because most people play by the rules. USAs would obliterate the rules, and cost the government a pretty penny.
But the real poison pill is this line: USAs should be highly flexible to allow Americans to save and invest as they see fit, including, for example, investments in a closely held business.
That sounds an awful lot like what Thiel did. Or, for example, a private equity fund manager could put his “carried interest” in a USA at the outset of a project. A CEO could contribute tens of thousands of shares of cheaply acquired stock options before the company goes public. A garage inventor—like Bill Gates once was—could value his company initially at $15,000 and put all of the stock into his USA. It’s not worth much now, but wait 10 years—Jackpot!
“Their tax avoidance potential would be infinitely greater. They would have the potential to exempt multibillion-dollar gains, even trillion-dollar gains, from taxation,” tax attorney Bob Lord and Morris Pearl, chair of Patriotic Millionaires, wrote in a Fortunecommentary.
“Allowing taxpayers to invest ‘as they see fit,’ could fuel stuffing…when an individual uses a tax-free account to acquire non-publicly traded assets at prices below fair market value,” Rosenthal told me in an email. (He and New York University law professor Daniel Hemel have written to the Senate Finance Committee, urging lawmakers to crack down on the practice.)
Whether Thiel’s Roth magic trick violates current IRS rules on “prohibited transactions” is a private matter for him and agency lawyers to hash out—but legal minds who have thought it through see some potential red flags. What’s more, the IRS has issued guidance that deems similar-sounding strategies “abusive” and says it views them as “tax avoidance transactions.”
Democratic presidential nominee Kamala Harris regularly asks Americans to imagine Donald Trump without guardrails. Well, imagine Roths without guardrails—larger contributions, no income cap, and no rules about how the funds can be invested. Roth IRAs in particular cost US taxpayers relatively little—about $14 billion a year—mainly because most people play by the rules. USAs would obliterate the rules, and in doing so, cost the government a pretty penny.
But this isn’t just about tax revenues. The bigger problem is how wildly inequitable America’s wealth and income distributions have become over the past four decades, a shift that started with the wealth-friendly tax cuts of the Reagan era. Just this week, the Congressional Budget Office reported that the average 2021 household income for the top-earning 1 percent of taxpayers was more than $3.1 million—42 times the average for the bottom 90 percent, according to an analysis of the data by Americans for Tax Fairness. That’s the most skewed income distribution since CBO began reporting on the data in 1979. Back then, the income disparity was 12 to 1.
America has ceased to be recognizable as a land of opportunity—or rather, one must now ask, a land of opportunity for whom?
USAs would be worth considering if Congress limited them to people with few assets who earn less than $100,000, for example, and imposed strict rules to prevent wealthy investors from gaming them for tax avoidance. As proposed by that nonprofit Trump knows nothing about, they would make our class divisions even worse. And that would truly be unaffordable.
Do you have $100 million? I don’t. Heck, I don’t even have $50 million! Which is why I’m not worried about the likes of President Joe Biden and maybe-president Kamala Harris and Rep. Barbara Lee and Sens. Elizabeth Warren, Ron Wyden, and Bernie Sanders—all of whom have proposed various levies on excessive wealth over the past five years—taxing my unrealized capital gains.
I do have unrealized capital gains. Maybe you do, too. My wife and I bought our house in Oakland, California, almost 20 years ago, and it’s worth more now than when we bought it. We also own shares of some stock funds that have appreciated over the years. Those paper gains are “unrealized” because we haven’t sold the assets. Unless they are sold, and the profits “realized,” they won’t be taxed under current law.
This gives America’s richest families a convenient way to avoid income tax. If you, like our thousand-ish billionaires, have vast stock holdings, you can have your tax lawyers and accountants arrange your affairs so as to minimize your realized income. Then, instead of selling long-held assets to fund your lavish lifestyle—and paying a capital gains tax of 20 percent plus a 3.8 percent surcharge known as the Net Investment Income Tax (NIIT)—you simply borrow against your holdings at a few percent interest, tops.
Guys like Bezos and Bloomberg and Buffett (who needs first names?) take advantage of this tactic, which is why ol’ Warren can accurately say he pays a lower overall tax rate than his secretary does. Per ProPublica‘s analysis, the wealth of the 25 richest Americans totaled $1.1 trillion at the end of 2018, but their combined 2018 tax bill? A scant $1.9 billion.
Several of the aforementioned wealth tax proposals, including Biden’s (which Harris generally supports), aim to shrink our obscene wealth gap by taxing the unrealized gains of the super-rich. But the $100 million Biden-Harris cutoff means that fewer than 10,000 people would be affected.
They arent talking about us. The capital gains tax has nothing to do with us. Aside from trying to reign in the uber greed of the already mega wealthy in our country. Trickle down economics failed. #harriswalz#capitalgainstax#taxtherich#99percent
The TikTok dad below, Dean, sums up the situation nicely: Taxing unrealized gains “sounds really ridiculous, and it’s very, very complicated,” he says. “But the key thing everyone needs to know, which is why I don’t care about it,” he says, is the cutoff: “I’d love to have this problem. It means I’m freakin’ worth $100 million!”
The people who are freakin’ worth $100 million oppose such a tax, of course. The New York Timesreports that a group of venture capitalists calling themselves VCs for Kamala has been whispering in her ear to dissuade her from trying to tax unrealized gains. In a survey, 75 percent of the group’s members reportedly agreed that doing so would “stifle innovation.”
Bob Lord, a tax attorney who advises Patriotic Millionaires, a group of affluent people seeking fairer tax policies, isn’t buying it. Wouldn’t that innovation-stifling argument “apply equally to their realized gains? And to their tax rates?” he asks in an email. “The logic would justify them having a negative tax rate, so we could spur innovation.”
“As I see it,” adds Lord (who helped write Rep. Barbara Lee’s Oligarch Act of 2023, and who has contributed to this publication) “any tax on the ultra-rich is significant to them only for how it impacts their wealth. Taxes don’t impact their spending decisions, their career decisions, college affordability, retirement decisions, or whether a spouse needs to work full time.”
Those taxes also won’t affect you if you have the following issue:
VCs for Kamala did not respond to questions I sent via their media contact, but those rich kids may not have to worry either. Congress has thus far been unwilling to touch unrealized gains, in part because, as Dean noted, it sounds ridiculous—even un-American—when applied to ordinary people.
I know. These aren’t ordinary people. But remember how, when Congress passed $80 billion in funding so the IRS would finally have sufficient resources to go after wealthy, sophisticated tax cheats? And remember how Republican lawmakers, including Donald Trump, widely (and falsely) shrieked that the Biden administration was hiring 87,000 new IRS agents to fan out and harass regular people just like you? Yeah, that was hogwash. But it was politically effective hogwash that helped set the stage for the GOP to claw back tens of billions of that funding as part of a subsequent debt ceiling deal.
Something similar would almost certainly happen if Congress got close to imposing a tax on unrealized gains. It’s simple politics: “We don’t feel in general that it’s fair to tax people when they don’t have the ability to pay,” explains Harvey Dale, an attorney who advises ultra-wealthy clients on tax matters. “Suppose I am a farmer. My family has owned this 1,000-acre spread for four generations, and in a good year I make $30,000 farming. But the land, wow, that could be worth $10 million now.”
(Note: That farmer, lacking $100 million in assets, would be unaffected by the Harris plan.)
The Supreme Court “is all but certain to strike down a tax on wealth, and the wealth transfer tax system we have has effectively been neutered through avoidance strategies.”
One could, of course, write exceptions into the law, “as long as you could figure out what all of those kinds of issues are,” Dale says. Or you could take a different approach: “Why don’t you say, in general, we won’t tax unrealized gains, but we’ll make exceptions and tax them—for example, if the asset in question is freely marketable, like securities, and we won’t do that for people below a certain level of wealth or income.”
As things stand, investors already get a sweetheart deal. When you profit from the sale of an asset today, you pay a far lower tax rate than you would if you made the money by working. Sometimes you pay no tax at all: Uncle Sam, for instance, lets a married couple pocket the first $500,000 in gains from the sale of their primary residence. (Sorry, renters.)
Stock is different. If you sell shares you’ve held at least a year, any profits are taxed at a rate based on your overall income. For 2024, a couple making up to about $94,000 pays no capital gains tax. From there up to $583,750, the rate is 15 percent plus that 3.8 percent NIIT on incomes north of $250,000. Families raking in even more pay 20 percent—23.8 percent with the NIIT.
That’s a great deal for people whose incomes derive largely from investments. It means that a couple with wage income of $1 million in 2024 owes the IRS about $321,000, whereas a couple with $1 million in investment income owes only $181,000. (These simple figures ignore tax credits, deductions, etc.)
Why structure our tax code this way? Some people say it’s to incentivize investment, but I’m skeptical. As long as the government isn’t taking 90 percent of your profits, people will keep investing. What else are you gonna do—shove your excess cash under the mattress? Bury it in the yard?
Another rationale, says Dale, who has taught tax at New York University’s law school for decades, involves “bunching.” If my job pays $100,000 a year and I work for five years, I pay 22 percent annually to the federal government. But suppose capital gains were taxed the same as wages. If an investor who’s held a bunch of stock for four years then sells that stock the fifth year for a $500,000 profit, their income is the same as mine, but because it came all at once, their tax rate would be closer to 28 or 29 percent. “So if you want the theoretical justification, it is to average out the bunching,” Dale told me.
For people who make more than $1 million a year, Biden has proposed taxing capital gains at the same top rate as ordinary income—currently 37 percent. Last week, Harris softened that proposal, saying she’d only raise the rate to 28 percent. She and Biden also both seem to support raising the NIIT to 5 percent on incomes north of $400,000. Which means wealthy investors would pay a total of 33 percent on realized gains.
But you don’t make $1 million a year, so never mind.
Trump hasn’t specified his plan for capital gains—maybe, as with health care, he only has a “concept of a plan.” But Project 2025, the Heritage Foundation blueprint created by conservatives from Trump’s first administration, proposes cutting the top rate to 15 percent and eliminating the NIIT. If that happens, America’s one-percenters will pay a tax rate on investment profits that’s less than half the rate they pay on their salaries. And it means wealthy families whose income comes largely from investments will pay a lower tax rate than workers who bring home the nation’s median pay: roughly $60,000 a year.
For hectomillionaires, people with $100 million or more, the Biden-Harris plan would impose a minimum tax of 25 percent on all income, realized and unrealized. But that faces long odds, because even if Congress passes it, the Supreme Court might slap it down.
As the Tax Policy Center’s Steven Rosenthal has written, in the case ofMoore v. United States, four of the justices “expressly declared that realization is a constitutional requirement” for taxation. If either Chief Justice John Roberts or Justice Brett Kavanaugh joins with their fellow conservatives, most of those wealth tax proposals would be in trouble.
Lawyers specializing in trusts and estates have long been engaged in “an ongoing, very complicated game to reduce the taxes paid by the wealthy.”
Tax attorney Lord sees a window: “The court is all but certain to strike down a tax on wealth, and the wealth transfer tax system we have has effectively been neutered through avoidance strategies,” he says, “so that leaves a tax on true economic income [including unrealized gains] as the only plausible option.”
Dale says he likes the Harris plan, and “it’s not clear that SCOTUS would declare unconstitutional a 25 percent tax on unrealized gains of people whose net worth is over $100 million, but it’s also not clear that SCOTUS would approve or sustain such a tax.”
That uncertainty, he adds, will affect how Congress views the proposal: “At least some senators and representatives would decide to vote against it because of its possible unconstitutionality. Others in Congress will vote against it because they will dislike such a tax.”
Dale’s NYU colleague, former Biden Treasury official and tax expert Lily Batchelder, is more optimistic about the Supreme Court sustaining a minimum income tax for extremely high-wealth individuals: “The majority in Moore expressed concern about how the petitioners’ arguments would deprive the government and the American people of trillions of dollars in tax revenue by eliminating a vast array of existing provisions, including multiple provisions that already tax unrealized income,” she notes in an email. “I think the case educated the justices about the ‘blast radius’ that would result if they read some sort of realization requirement into the Constitution.”
It’s always been somewhat of a challenge to effectively tax the superwealthy, who wield political power and guard their hoards as jealously as Smaug, the Tolkien dragon. But Congress isn’t without options. It could, as Sens. Wyden and Angus King have proposed, restrict abusive trusts that allow billionaires to transfer massive sums to their heirs without paying a dime in tax. And lawmakers could cap federally subsidized retirement accounts to prevent wealthy retirees from taking excessive government handouts.
They also could do away with carried interest once and for all and strengthen the rules for Roth IRAs—retirement accounts meant for the middle class—that have famously allowed Silicon Valley’s Peter Thiel to parlay a $1,700 retirement fund contribution into billions of tax-free dollars.
And they could, as Biden has proposed, eliminate the socially corrosive “step-up in basis” rule: Suppose your father bought $5,000 worth of stock in 1960 and now it’s worth $5 million. If he dies and leaves it to you, under today’s rules, the “cost basis” of the stock—what it cost him originally—resets to the current market value. Boom! Your family just sidestepped taxes on almost $5 million in investment profits.
His estate wouldn’t have to pay any tax on that transfer, either: As of 2024, the IRS lets a couple give their kids up to $27.2 million, free of any gift or estate tax. This generous exemption is yet another rule that Congress could target. In fact, it’s set to revert to half that amount at the end of 2025, so I guess we’ll see whether our lawmakers will stand up to the oligarchs.
“There are $5 trillion of offsets in the president’s budget that raise revenue exclusively from large corporations and individuals earning more than $400,000 in income,” Batchelder points out. “Every member of Congress has different views about which of these options are most appealing, so the most doable reforms will depend on who are the marginal votes in Congress after the election, but there are many, many options.”
Dale figures the best way to shrink the wealth gap is to target inheritances—closing loopholes, restricting trusts, and generally strengthening the rules on intergenerational wealth transfers, which are taxed at only about 2 percent overall, per Batchelder’s 2020 analysis. The wealth industry will find workarounds, and you’ll never get a perfect system, he says, but you could make inheritance taxes harder to circumvent.
“A nontrivial portion of my practice was estate planning,” a field that has long engaged in “an ongoing, very complicated game to reduce the taxes paid by the wealthy,” Dale says. “It would be sweet, I suppose, to say, here is one simple thing that could be done that your readers can understand. But the loopholes are very, very sophisticated. If I tell you that the right thing to do is to repeal 664(c)(1), your eyes would glaze over. But there are trillions of dollars in that simple thought.”
It’s fair to say that Michelle Obama stole the show at the Democratic Convention on Tuesday. (Husband Barack was on point in noting how hard an act she was to follow.) And to a journalist like me who covers wealth and inequality, one line in particular stood out. Listen:
Michelle Obama: She understands that most of us will never be afforded the grace of failing forward. We will never benefit from the affirmative action of generational wealth. pic.twitter.com/ywBjdwZl3E
Theaffirmative action of generational wealth. That’s a smart reframing of a longtime conservative hobby horse.
Republican politicians and right-wing media have regularly attacked programs designed to counter the generational impacts of government-sanctioned discrimination in housing, education, and veterans benefits. Now they’re targeting diversity, equity, and inclusion programs—see JD Vance’s recently introduced “Dismantle DEI Act“—and trying to brand Kamala Harris a “DEI hire.” That’s a laughable assertion. (New York Times columnist Lydia Polgreen argues that the moniker applies more aptly to Vance.)
But the critics of DEI and affirmative action want to have their cake and eat it too. For example, if you, like our Supreme Court, think the use of race as a factor in college admissions should be illegal, that’s your prerogative. But I hope you are similarly inclined to outlaw the practice of elite colleges giving an admissions boost to children of alumni and to students (like Jared Kushner) whose parents are major donors. Because isn’t that, too, a kind of affirmative action?
In just a handful of words, Michelle Obama managed to convey a simple truth, says Dedrick Asante-Muhammad, president of the Joint Center for Political and Economic Studies, a Washington think tank that focuses on the racial wealth-and-opportunity gap: “It is not those asking to break up concentrated wealth and opportunity that are asking for an unfair advantage, but rather those who are hoarding concentrated wealth.”
“Most of us,” as Obama noted, “will never benefit” from generational wealth. And that’s true of everyone, but even truer when you are Black or Hispanic.In the Federal Reserve Board’s 2019 Survey of Consumer Finances (SCF)*, about 47 percent of white respondents said they’d either received an inheritance or expected to receive one. Their median inheritance expected was $195,500 (in 2019 dollars).
Only 16 percent of Black respondents had received or expected an inheritance—and their median expectation was about half the white figure. Less than 12 percent of Hispanic respondents had received or expected an inheritance.
The disparities are similar when you look at federally subsidized retirement savings, which, according to the congressional Joint Committee on Taxation (JCT), will cost US taxpayers a whopping $1.9 trillion from 2020-2024. Most of that cash goes to the wealthiest 10 percent of Americans, who tend to be, yep, pretty white.
In 2021, the JCT identified 8,000 Americans with Individual Retirement Account (IRA) balances in excess of $5 million who were still getting tax breaks for their annual contributions—which is “shocking but not surprising,” noted Senate Finance Committee chair Ron Wyden. Peter Thiel, ProPublica reported, even managed, using questionable tactics, to amass a Roth IRA worth $5 billion.
Affirmative action for the rich.
According to the latest (2022) SCF,only 35 percent of Black families and less than 28 percent of Hispanic households even had a retirement account, compared with 62 percent of white families. The accounts of those white families were worth over $380,000 on average, more than triple the Black and Hispanic savings—and again, these numbers don’t account for the fact that a large majority of Black and Hispanic households have no private retirement accounts at all.
Then there’s land ownership—see “40 Acres and a Lie,” our acclaimed multimedia package exploring how the few Black families who received land reparations after the Civil War then had their acres cruelly rescinded a year and a half later. And consider these passages on the Homestead Acts, from a chapter of my 2021 book, Jackpot, titled “Thriving While Black.”
The two acts, passed during and after the Civil War, granted 160-acre parcels of public land—a foundation for generational wealth—to families willing to stake out the plots and make improvements. But the timing and circumstances made it extraordinarily difficult for Black Americans to participate:
It was a once-in-a-lifetime bonanza for white fortune-seekers. “The acquisition of property was the key to moving upward from a low to a higher stratum,” wrote author Everett Dick. “The property holder could vote and hold office, but the man with no property was practically on the same political level as the indentured servant or slave.” […]
Between the two acts, about 270 million acres of farmland—14 percent of the total landmass of the continental United States—was granted to 1.6 million white families, but only 4,000 to 5,000 Black families. [University of Michigan professor Trina] Shanks calculates that more than 48 million living Americans are direct descendants of those Homestead Act beneficiaries. Which means there’s a greater than one-in-four chance your forebears benefited directly from the biggest public-to-private wealth transfer in American history—if you’re white, that is.
Affirmative action for the rich.
Obama hit the nail on the head. Asante-Muhammad says he was struck by her simple acknowledgement “that affirmative action for the privileged happens,” though “I wish there could have been a follow up to re-emphasize why programmatic affirmative action to advance more equal opportunity is necessary.”
But “it felt good,” he adds, “to hear a political speech that connects so personally with my political ideals, and to the challenges of the racial wealth divide and the action and ideals needed to bridge it.”
*I used 2019 numbers here because the 2022 inheritance data was only available in raw form.
Mormons would probably be psyched. The Republican Party less so.
I’m talking about what would happen if we embraced the idea, proposed by Donald Trump’s running mate, Ohio Sen. JD Vance—isn’t he funny?—of empowering families by giving parents of young children an extra vote for each child.
Besides being likely unconstitutional (see the unanimous 2016 Supreme Court ruling in Evenwel v. Abbott, which upheld the 14th Amendment principle of “one person, one vote”) such a policy would be difficult to implement. Who gets the extra votes if there’s an odd number of kids and/or the parents are estranged or have opposing views? Who votes on behalf of stepkids—do they count? Adoptees? How about kids living with their grandparents? Noncitizen parents? Parents with Green Cards? Could undocumented parents vote on behalf of US-born offspring? And how would you verify all of it?
To be fair, in an interview over the weekend, Vance clarified that his proposal was simply a “thought experiment.” Okay then! Let’s think it through.
Assuming this proposal were legal and workable, whom would it benefit? Certainly the Mormons, who are known for prolific procreation (in 2014, according to a Pew Research report, Mormon couples ages 40-59 had an average of 3.4 children vs. 2.2 for all Christians and 2.1 nationally—they also famously have a history of having too many spouses.) Mormons tend to be conservative and vote Republican. But only about 1.2 percent of Americans identifed as Mormons in 2022, per the Washington Post. So who else might benefit?
Predicting voter preference and its impact on a given race is complicated and involves various interrelated factors: One must consider a given group’s cohesiveness, political tendencies, and likelihood of turnout, in addition to age, education, income, and geographical concentration—for example, Michigan’s Somali diaspora, Hawaii’s large Pacific Islander population, and Mexican Americans in the Southwest.
America’s young parents are more ethnically diverse than the broader population, and most minority groups lean Democratic—but turnout wold be key.
To these factors we can now add fecundity.
To make sense of all this stuff, you’d need a pro, so I called up William H. Frey, a senior fellow at the Brookings Institution and US Census expert who has researched urban populations, migration, immigration, race, aging, and political demographics. He’s also the author of the 2018 book,Diversity Explosion: How New Racial Demographics are Remaking America.
I also poked around for useful data. The Census Bureau’s 2023 Current Population Survey breaks down, by race and income, households with children under 18. That’s useful, because income is a rough proxy for education, and families with less education tend to have more children, Frey told me.
Non-Hispanic whites are significantly under-represented among parent households with incomes of less than $75,000—which account for 38 percent of all families with young children—while Latinos are substantially over-represented. In the slightly larger and more educated middle tier, households with $75,000-$199,999 in income, Asians and non-Hispanic whites are slightly over-represented while Black and Hispanic households are slightly under-represented. In the high-income tier ($200,000-plus), non-Hispanic whites and Asians are strongly over-represented while Black and Hispanic households are strongly under-represented—but only 17 percent of all families with young kids fall into this high-income, high-education, and likely high-turnout group.
The US has 3.5 million non-Hispanic, mixed-race kids, whom Trump managed to insult by asking, of Kamala Harris, “Is she Indian or is she Black?”
Slice and dice as you will, the upshot is that America’s youth, and their parents, are more ethnically diverse than the broader population. Non-Hispanic whites are 58 percent of the population, but less than half of kids under 18 are white only. Fourteen percent of kids are Black only, echoing the Black share of the US population. Ditto Asian kids (6 percent vs. 6.5 percent). But Latinos, representing 19.5 percent of the overall population, account for more than a quarter of minor children.
As of last year, non-Hispanic white families had 35.2 million minor children, whereas Asian, Black, and Latino families—all groups that tend to vote Democratic, Frey says—had 33.4 million children combined. (There were also 3.5 million non-Hispanic mixed-race kids—whom Trump may have managed to insult by asking, of Kamala Harris, “Is she Indian or is she Black?” Because one can’t be both!)
Trump’s supporters tend to be older and whiter, whereas most voting-eligible parents of young children would fall into the 25-44 age categories, which are more ethnically diverse, as this chart Frey put together demonstrates. (Scroll over the bars for exact percentages.)
Given our Electoral College rules, geographical clustering matters for the presidential race. Ethnically diverse states such as Texas and California, as Frey points out, "are going to have a bigger share of their voting age population with children and minority children. So that can help bolster the minority vote." Also, a sizeable share of America's Black population resides in red and purple states. And again, minority voters tend to favor Democrats.
"The key issue is turnout," Frey says. "High turnout is largely old people, college educated whites. Not so much for young people. And not so much for most minorities, except in some elections, like when Obama was running." (Note: This could be one such election.)
There's also an X-factor to consider: Might the promise of extra votes serve as an incentive for parents who might not otherwise do so to get out and exercise their patriotic duty, potentially narrowing ethnic and educational turnout disparities?
Frey was too busy to help me conduct an official analysis, but his overall impression is that Vance's idea would likely benefit Democratic candidates and priorities. "The whole thing is a bit hard to execute anyway," he says with a laugh. "Who’s gonna check? They accuse everybody of voter fraud if they just do normal voting. What happens if they do this kind of thing?"
Have you seen any of those clips from Donald Trump’s rambling press conference this past Thursday? If not, count yourself lucky. Standing at a Mar-a-Lago podium, Trump did what he always does: equivocated, meandered among subjects, spoke in half-sentences full of non sequiturs, and lied relentlessly. Challenging questions were in short supply—a media fail. Then again, maybe just showing up was the bigger fail, given Trump’s inability to engage honestly.
But one has to try. Calling Trump out is our professional responsibility. The women who grilled him onstage at the National Association of Black Journalists conference—Harris Faulkner, Kadia Goba, and Rachel Scott—set a good example.
Apparently not enough of the Mar-a-Lago journalists got the memo.
Their questions weren’t mic’d, so they were barely audible in the video. But I cranked up the volume and listened carefully, transcribing as accurately as I could. Trump took roughly 40 questions. Most were uncritical softballs. Here’s a sampling, paraphrased:
Does he consider Kamala Harris more talented than Joe Biden and Hillary Clinton?
Does he think Harris is worse than Biden?
What does he think about Harris not picking Josh Shapiro for her VP?
Is he worried about the size of Harris’ crowds?
Has he followed this whole thing about Harris dating Willie Brown?
Is his ear fully recovered? Is there a scar?
Could he talk about his upcoming interview with Elon Musk?
Was Steve Bannon’s imprisonment politically motivated?
Would he consider pardoning Hunter Biden?
There was a smattering of policy questions—which is fine, but lightweight. Some examples (these are semi-verbatim; watch the video for Trump’s full answers):
“Harris supports rescheduling marijuana and says no one should go to prison for marijuana. Do you agree with that?” (“As we legalize it, I start to agree a lot more.”)
“Do you support continuation of tax credits for EVs?” (“They want everybody to have an electric car. We don’t have enough electricity.”)
“What do you make of reports that Harris said she might consider an arms embargo on Israel?” (“I’d be against that.”)
“Did the use of an AR-15 gun by your would-be assassin change your view on people’s access to that weapon?” (“No.”)
“How will you vote on the Florida amendment [that would codify abortion rights in the state constitution?]” (“I don’t want to tell you now.”)
“There are other things the federal government can do, not just a ban [on abortion]. Would you direct your FDA, for example, to revoke access to mifepristone?” (“You could do things that would supplement, absolutely…But you have to be able to have a vote.”)
Only a handful of questions were at all confrontational:
“Kamala Harris’ father is Jamaican. She went to a historically Black college. How has she only recently decided to be Black?” (Trump equivocated and doubled down—again.)
“What is your response to President Biden when he says he fears there wouldn’t be a peaceful transfer of power if you lose?”
In his response, Trump misleadingly claimed there had been a peaceful transfer of power “last time.” Another reporter, I believe it was Maggie Haberman of the New York Times, came back to that:
“You think the last time was a peaceful transfer of power?” (No, Trump replied, because the January 6 protesters “were treated very unfairly.”)
Also Haberman: “When you were president, you pardoned [inaudible] drug dealers and violent felons, including one man who told a rabbi, “I am going to make you bleed.” How is that different from [inaudible]? (“We had commissions…They would recommend to me certain pardons for certain people.” In fact, as Mother Jones has reported, Trump threw the standard clemency process out the window.)
Here are 22 questions—I could easily come up with 22 more—that journalists should be asking this candidate, or at least asking of him. Granted, it might be the last time Trump ever took a question from you, but it’d be worth it.
Partisan divisions A Pew analysis shows voters are about evenly split in favor of Democrats and Republicans. Yet you’ve called Democrats “treasonous,” “un-American,” “crazy,” “loco,” “rage-filled,” and “the party of crime.” You retweeted a video in which a supporter said, “The only good Democrat is a dead Democrat.” You regularly use “us vs. them” rhetoric. Why should voters support a candidate who seeks to divide Americans?
Migrant crime You’ve gone around claiming that nations are emptying out their jails, prisons, and, in your words, “insane asylums,” sending “millions” of criminals and mental patients across our southern border. That’s a pretty outrageous lie, and your claim that undocumented migrants are driving a crime wave is demonstrably false. Why do you insist on repeating these falsehoods?
School vaccinations You’ve said that you will defund any school with a vaccine mandate. Are you only talking about Covid vaccines, or also the routine childhood immunizations that prevent catastrophic illnesses such as polio and measles?
Stochastic terrorism The FBI says it has found no evidence that the man who shot you and others in Pennsylvania was politically motivated. He was, in fact, a registered Republican voter. But you and your campaign surrogates, including your sons, keep saying the Democrats tried to kill you in Pennsylvania—a baseless claim that experts have told Mother Jones will fuel political violence. Why do you and your surrogates keep making this false claim?
January 6 You’ve said you would pardon people who participated in the US Capitol attack on January 6, 2021, using words like “patriots” to describe members of a mob that beat police officers with hockey sticks, flagpoles, and fire extinguishers; crushed cops in doors; and sprayed them with bear spray. How can you then say you are pro-police and pro-law-and-order?
Taxing tips You’ve proposed to eliminate income tax on tips. How is that fair to untipped low-wage workers like grocery store clerks and delivery drivers? Would you also support raising the federal minimum wage, which has been stalled at $7.25 an hour since 2009? (Harris, who embraced Trump’s proposal on Saturday, favors raising the minimum wage.)
Dehumanization of immigrants Your own businesses have knowingly employed undocumented workers over the years for everything from landscaping and maintenance to modeling and hospitality services. Why must you now go around claiming these people you depended upon are “poisoning the blood of our country”?
Mass deportations Economists question your plan to deport 11 million undocumented people, including otherwise law-abiding families who have been in the US for decades, working, owning homes, and paying taxes. They say mass deportations would shrink the US economy 6 percent over 20 years and cost US workers about 968,000 jobs. We’d lose almost $100 billion a year that those families pay in taxes. The agriculture, construction, and hospitality industries rely on their labor, and migrants commit fewer crimes than native-born Americans. Why do you think uprooting established families is a good policy?
Border policy Congress recently put forth a bipartisan border bill that gave Republicans much of what they’d long been asking for. It was a huge policy victory for your party, but you put the kibosh on it because, as you admitted, you wanted to use the border issue against Biden. How do you justify putting your campaign ahead of your party’s hard-fought goals?
Family separations Illegal immigration has bedeviled presidents of both parties. Yet on your watch, migrant parents were forcibly separated from babies and young children, an astonishingly cruel policy with lasting effects on good families. How does showing up on the border, or even crossing illegally, justify such a heartless response—and why does its architect, Stephen Miller, remain in your circle of advisors?
Clean energy You have vowed to claw back clean energy funding passed under the Biden administration. But that funding has sparked a domestic manufacturing boom in red states. The southern “battery belt” is booming. Shouldn’t a Republican candidate celebrate that?
Dirty energy You approached oil executives asking for $1 billion in campaign contributions, saying, if elected, you would lower barriers to drilling and make them tons of money. Americans are not blind. Climate change is real and causing increasingly worse storms, fires, droughts, and floods like the ones in the Southeast this week. It’s driving home insurance prices through the roof. How can encouraging more oil extraction be a sensible policy given the disastrous result of burning fossil fuels?
Corruption The mantra during your 2016 campaign was “drain the swamp.” But your cabinet picks—people like EPA administrator Scott Pruitt, a man openly hostile to environmental protections—were objectively swampy. You and an unprecedented number of your associates have been investigated, charged with crimes, and in many cases convicted. How can you speak of draining the swamp when your administration embodied it?
Project 2025 You flew on a private jet with Kevin Roberts, the architect of Heritage Foundation’s Project 2025, and praised him—and the project—at a Heritage conference. Some 140 people from your administration, including six of your cabinet chiefs, worked on Project 2025. How could you claim you knew nothing about it and that it won’t affect your presidential agenda?
Abortion By saying abortion should be left to the states, you are in effect supporting the harshest restrictions any state imposes. Some don’t allow exceptions for rape and incest, and even in states with exceptions for a mother’s health, doctors are delaying emergency abortions until their patients are near death. How do you propose to protect these women?
Race Following up on the earlier race question, Kamala Harris has always identified both as Black and South Asian. You asked, well, “Is she Indian or is she Black?” Don’t you think this “either or” language might be insulting to the 9 percent of American adults who identify as multiracial?
Pandering to Christian voters At a recent conference, you urged Christians to get out and vote, saying they wouldn’t have to vote anymore after that. “It’ll be fixed,” you said. What will be fixed? Abortion? Elections? Please explain your meaning.
Nicknames You’ve called your opponent “Laughin’ Kamala,” but it seems like many people appreciate her joyfulness. Do you see laugher as negative? Separately, I’d like to know why you think it’s okay to call her “Kamabla.”
Military service JD Vance and others in your inner circle have targeted Tim Walz over his military service, but Walz volunteered and served for 24 years. You took multiple deferments from the Vietnam draft, claiming bone spurs based on a diagnosis the doctor’s daughters now say was phony—a favor for your father. You dodged your duty, so how can you justify going after Walz?
Economy The Biden administration has bested yours on several key economic measures: He’s overseen lower unemployment, more robust wage growth, more new jobs, more domestic manufacturing, higher household incomes, lower child poverty, and fewer uninsured Americans. His big problem has been inflation, but that was also a global problem triggered by the pandemic, supply chain disruptions, price-gouging, and soaring energy prices from Russia’s war on Ukraine. Economic growth was about the same during your two administrations. So how can you say yours was the “greatest economy” while Biden has done a “poor job”?
Foreign influence How can voters expect you to deal even-handedly with the Saudis when they provided $2 billion in financing to your son-in-law?
Mendacity Voters are not naïve. Every politician bends the truth and some lie on occasion. But the nation’s fact-checkers can barely keep up with you. You’ve been lying this entire press conference. Why are we even here?
The internet has been burning up this past week with the many, many faux pas—faux paws?—of Donald Trump’s running mate, JD Vance, what with his “childless cat ladies” thing, his endorsement of a reprehensible book by a reprehensible guy, and the foreword Vance wrote for yet another book, by Project 2025 architect Kevin Roberts, even as Trump was trying to distance himself from that political dumpster fire.
It is fun, however, to take some of Vance’s more ridiculous assertions at face value, such as his claim that “the entire Democrat Party is like this childless cabal of people who don’t really care about the future.” (You didn’t think the Harris campaign was going to let that one go by, did you?)
Unearthed video: JD Vance calls Democrats a “childless cabal of people who don't really care about the future” pic.twitter.com/dfWKajTc7y
Transportation Secretary Pete Buttigieg—whom Vance namechecked as “childless” even as Buttigieg and his husband were in the midst of adopting a child—made the case quite eloquently to Jon Stewart that being childless and caring about your country’s future are not mutually exclusive. Exhibit A: The young people who volunteer for military service. Watch:
And then it’s worth asking: Is there even truth to this notion of Democrats being childless? I wasn’t about to waste my time looking up every member of Congress, but I did want to run a little truthiness test. So I looked up the parental status of every member of the House of Representatives from my liberal state of California—also the nation’s most populous state.
California has 52 House members: 40 Democrats, 12 Republicans.
Forty percent of those Democrats are women and only 16 percent of the Republicans are. Given the rigors of public office and the fact that moms are often saddled with the lion’s share of child care duties, you might then expect an overall higher rate of childlessness among the Democratic politicians. But you would be wrong.
With the caveat that one of the Democratic women has stepchildren, not biological ones, 85 percent of the Dems have kids, as opposed to 83 percent of the Republicans. If you exclude Rep. Sydney Kai Kamlager-Dove’s stepkids, which isn’t very nice, it becomes even: 83 percent for both.
For a reality check, I also looked at Georgia’s House delegation—9 Republicans, 5 Democrats. All of them have had kids except one: a Republican.
Let’s break down those numbers. On the Democratic side, 88 percent of the male reps have kids and 81 percent of the women do—three-quarters if you exclude the poor stepkids. The Cali Republicans have only two women in their caucus—both with kids—while 8 of the 10 men have them. (And, to be fair, one of the childless ones was just recently married.)
The remaining childless Republican dude, a MAGA type known for his adamant opposition to abortion rights and LGBTQ rights, tried to tell local police back in 1993 that he and the prostitute he was doing stuff with in his car were “just talking.” (He later admitted they were having sex.) But debauchery has no party affiliation: In 1986, one of the childless male Dems had been cited by police for soliciting prostitution.
The other two childless Democratic men are openly gay, and of the four Democratic women with no biological children, one is 35 and unmarried—though in a relationship, so who knows? We don’t know the story with the others, and even Vance concedes that plenty of people who want kids can’t have them for all sorts of reasons.
So what is this guy even talking about? Based on my California House sample, Dems are no more likely to be childless than Republicans are. I would predict the national numbers aren’t much different—there’s a fun weekend project if any of my media colleagues want to take it on.
For a reality check, though, I looked at Georgia’s House delegation—nine Republicans, five Democrats. Republican Andrew Clyde, a firearms dealer, is the only one of them who hasn’t had kids, although he does have a doberman named Kit. Georgia Democratic Rep. Lucy McBath, who is Black, used to have a child. She ran for Congress only after her son, Jordan, was murdered at a gas station by a 46-year-old white man complaining about Jordan and his friends’ “loud music.”
The upshot of this little experiment, I suppose, is that if America’s childless are indeed some sort of cabal, it would appear to be pretty minor—and bipartisan. But a hearty thank you to JD for making it all possible.
“You can tell a lot by a laugh,” Donald Trump told supporters the other day, reviving a weird and arguably very sexist right-wing criticism of his new White House rival, Kamala Harris. “I call her Laughing Kamala. You ever watch her laugh?… She’s crazy. She’s nuts.”
Trump then proceeded to call Nancy Pelosi crazy, saying that “she turned on [Biden] like a dog.”
Like a dog.
But this is not a story about Trump’s deployment of specific types of insults against women (he bullies men, too), such as when he called Hillary Clinton “shrill.”
This is a story about laughter.
Shortly after Trump made his comments, his stalwart pal, the Fox News host Sean Hannity, piled on, saying on his show that voters “seem to detest” Harris on account of her readiness to laugh—or maybe because of the way she laughs? It’s hard to tell. But Hannity clearly aims to convince his viewers to detest Harris, if they don’t already.
Hannity: Here’s just one reason voters seem to detest Kamala Harris
Hearing Trump and his cronies insult Harris’ hearty chuckle—which his campaign also impugns in this anti-Biden ad—got me thinking about how I had never, ever heard Trump laugh.
It turns out I wasn’t the first journalist to have that thought. Several media colleagues have made this observation in the past, but if Trump wants to weaponize his opponent’s noteworthy laugh, we should probably talk about that. And Trump’s lack of one.
Suppose we take Trump’s statement at face value: You can tell a lot about a person from their laugh. Well, I’m just one guy, but to me Harris’ chortle suggests she’s a fun-loving individual. Is that such a terrible leadership trait?
Laughter is pretty much universally seen as positive. Indeed, the list of prominent people who have spoken and written of the value of laughter is long. It includes Catherine the Great, Charlie Chaplin, Charles Dickens, Robert Frost, Kahlil Gibran, Martin Luther King Jr., William Shakespeare, Gloria Steinem, Virginia Wolfe, and on and on. Perhaps more relatable to Trump would be Andrew Carnegie, who is credited as saying: “There is little success where there is little laughter.”
Less relatable for him, perhaps, would be this quote from W.E.B. DuBois: “I am especially glad of the divine gift of laughter: it has made the world human and lovable, despite all its pain and wrong.”
“It stayed with me, that I’ve never seen him laugh. Not in public, not in private…,” James Comey said. “I never saw anything that resembled a laugh.”
What does it mean when one lacks this gift? I emailed Bandy X. Lee, an outspoken psychiatrist Mother Jonesprofiled in 2022 whose new book is titled, The Psychology of Trump Contagion: An Existential Threat to American Democracy and All Humankind, to get her take.
Trump’s “rigidity and lack of flexibility, deriving from a state of pathology, appear to underlie his lack of humor more than anything else,” Lee replied. “In other words, it is not just a difference in style but a defect. This may belie his ‘entertaining’ persona, through which he makes others laugh, but this is the ‘charming’ façade of a dangerous personality with predatory intent, not someone with true leisure of mind who can laugh at reality.”
Trump’s estranged niece, the psychologist Mary Trump—whose 2020 family memoir, Too Much and Never Enough: How My Family Created the World’s Most Dangerous Man, was a huge best-seller—also touched on the subject of Donald’s mirthlessness in a Slate interview with journalist Virginia Heffernan. When Heffernan asked Mary whether she thought her Uncle Donald was happy, she replied:
There’s no way he could be happy because the myths that have been created about him and that he’s perpetuated and believes about himself are always in constant danger of disintegrating. On some deep level, he knows that. He’s very much always living in the moment. So how can you be happy?
And how can you be happy if you don’t laugh or appreciate humor? What that says to me, because my grandfather also didn’t laugh, is that laughing is to make yourself vulnerable, it’s to let down your guard in some way, it’s to lose a little bit of control. And that can’t happen. That is not allowed to happen.
And here’s another quote, from the acclaimed author Maya Angelou. “Don’t trust people who don’t laugh,” she once told a crowd at the University of Buffalo in New York, adding, “I don’t.”
In a 2018 interview with ABC News host George Stephanopoulos, the former FBI Director James Comey reflected on this unusual trait of his former boss, Donald Trump, who seems to enjoy making supporters crack up, but rarely does so himself. “I was struck by it. So struck by it, it stayed with me, that I’ve never seen him laugh. Not in public, not in private…,” Comey said. “I never saw anything that resembled a laugh.”
After Trump fired Comey, that thought stuck with him, he said, “So I went and tried to find examples of videos where he’s laughing and I could only find [what] really wasn’t a genuine laugh.“
I looked around, too. Donald Trump is among the most filmed and scrutinized people on the planet, so if he laughed a lot we would know about it. But he really seldom does, publicly anyway. I could find only a small number of clips, and in most of them he only sort of laughs, or laughs briefly. There are even fewer in which his laughter seems genuine—such as this one, wherein Jimmy Fallon roasts Trump pretty hilariously, and who wouldn’t crack up in that situation?
But what seems to prompt the lion’s share of his scant public laughs should give voters pause. I’m all for inappropriate levity, but it’s problematic when so much of a powerful man’s laughter involves mocking people or laughing at someone else’s misfortunes. In this clip, he laughs when a rallygoer yells out that we should shoot migrants coming across the southern border.
I cannot vouch for the veracity of this next clip, but Trump seems to get a good laugh at an impersonator mocking President Joe Biden over his rally sound system.
In this one he appears to laugh at his supporters chanting—not of Hillary Clinton, but of Sen. Dianne Feinstein, who had severe cognitive impairments—”Lock her up!”
And here is perhaps his most genuine laugh of all, a clip that takes us back to where we started: a powerful woman being equated to a dog.
But as Kat Abughazaleh, our video essayist, pointed out recently, the right doesn’t yet seem to have come up with a better line of attack on Harris than “she laughs too much.”
Correction: An earlier version of this story listed Maya Angelou as 86 years old. Angelou died at age 86, in 2014.
Campaign finance disclosures are made public too ridiculously slowly to be of much use for real-time political analysis, but they do reveal some general trends in terms of who supports whom, and how rich they are.
I previously reported that, according to Federal Election Commission data through May 1—before Donald Trump’s criminal conviction, Biden’s disastrous debate performance, or Saturday’s assassination attempt—Trump was getting less than one-third of his contributions from small donors (people who gave less than $200), whereas the 100 top donors (all very, very rich) favored Republicans by a margin of 3 to 1.
That hasn’t changed per the latest data, most of which only gets us through May 31—which is still before all of the mayhem mentioned above. With the new numbers, the Top 100 still favor Republican groups and candidates, in dollars given, by a nearly 3-to-1 margin.
One notable difference involved a reshuffling among the Top 5, who have given overwhelmingly to Republicans and their causes. The lead position in the last round was held by billionaire couple Janine and Jeffrey Yass—he’s a cofounder of Susquehanna International Group (an investment firm) and a major TikTok investor. From his contribution history, it’s clear that Yass wasn’t much of a Trump supporter, though Susquehanna owned a stake in the special purpose acquisition company that merged with Trump Media.
The latest (and likely current, though not for long) top donor is a major Trump backer. That’s banking dynasty heir Timothy Mellon—a “reclusive plutocrat,” as independent journalist Judd Legum wrote in his Popular Information Substack, who over the past 12 months has given $25 million to American Values 2024, a Super PAC supporting Robert Kennedy, Jr. and then turned around and donated a whopping $50 million to the Trump Super PAC Make America Great Again Inc. the day after a jury found the former president guilty of 34 felonies.
At last count, the Top 100 had doled out $933.5 million, only 22 percent of which went to solidly Democratic candidates and causes.
In all, this election cycle, Mellon has given more than $115 million to Republicans, including $76.5 million to MAGA Inc. He also, as Legum noted, has donated $4 million to Sentinel Action Fund, a Super PAC created by Heritage Action, a subsidiary of the Heritage Foundation, whose controversial Project 2025 was created as more or less a blueprint for a second Trump term—though Trump, incredibly, claims no knowledge of it.
Moreover, in 2020, Mellon gave $20 million to America First Action, a Super PAC run by America First Inc., a nonprofit that claims in its IRS filings it is “bipartisan,” but listed as its board chair Linda McMahon. That’s the WWE mogul Trump appointed to run his Small Business Administration. Linda and her husband, Vince McMahon, are No. 17 on the Top 100 donors list, giving more than $11 million so far to Republican candidates and causes during the current election cycle. Nonpartisan indeed.
At last count, the Top 100 had doled out a total of $933.5 million to candidates, party committees, and outside groups. Only 22 percent of it went to solidly Democratic candidates and causes, while 64 percent went to solidly Republican candidates and causes.
President Joe Biden’s campaign committee raised a total of about $231 million, of which 42 percent came from small donors giving less than $200. Trump’s campaign committee reported about $196 million in donations, 31 percent from under-$200 donors. The Trump campaign also reported about $193 million from outside groups, while the Biden campaign reported roughly $160 million.
So that’s where we are—or rather, were. So much has changed, so quickly, in this race. Trump’s conviction, for which he showed only contempt, and no remorse, only seemed to boost his status with MAGA die-hards. Meanwhile, ever since that unforgettable June 26 debate, top Democratic donors have been flipping out about Biden, who keeps insisting he’s in for the long haul.
And then came the attempt on Trump’s life, which has energized his already frenetic base, and could fuel his grassroots fundraising efforts.
On Sunday, less than 24 hours after a 20-year-old man fired an AR-15 at the Republican nominee, wounding him slightly, Trump’s campaign was already sending out pleas like the following, which landed in a colleague’s inbox at 2:51 pm ET that day:
Just when the IRS was starting to get its mojo back, the Supreme Court had to go and throw a wrench into the works.
By now, most civic-minded Americans will have heard about the recent high court rulings that threaten to crush the administrative state, crippling the government’s ability to enact and enforce critical regulations that advance the nation’s interests and protect her citizens.
My colleague Jackie Mogensen recently described how a 2023 Supreme Court decision limiting the EPA’s jurisdiction has made way for polluted rivers. June’s rulings bode far worse, for both the natural environment and efforts to combat climate change. Colleague Nina Martin has examined how the new rulings will be weaponized to gut reproductive rights. The New Republic’s Timothy Noah covered how they may affect the banking sector—and the economy. Others have looked at impacts on health care. And so I set out to determine the extent of the chaos the court’s rulings will unleash on the federal tax system.
Short answer: Nobody knows, but it won’t be pretty.
Loper “unleashes so much chaos,” says Georgetown Law professor Brian Galle. “I think you will see a massive wave of antiregulatory lawsuits.”
Tax law is extraordinarily complicated. So much so that few lawmakers have any hope of understanding its nuances. Attorneys who specialize in tax, as one of my sources points out, tend to go beyond law school to obtain a master’s degree. Tax is also a realm that demands long-term planning by individuals and businesses. Stability is important. But with the Supreme Court latest actions, “what used to be fairly settled law now becomes potentially unsettled,” says attorney Harvey Dale, who has taught tax at the New York University School of Law for more than four decades. “It’s a very, very bad outcome.”
Two rulings in particular “will bring much more litigation into the federal courts. I’m talking hundreds, maybe thousands of litigations trying to take down regulations, some of which may be 50 years old. So that unsettles planning for the entire nongovernmental sector,” Dale says.
First and most notable is Loper Bright Enterprises v. Raimondo, wherein the Supreme Court majority killed the so-called Chevron deference. Chevron is the legal standard that has long guided career experts at federal agencies as they carried out the intent of Congress, translating broad legislative strokes into enforceable regulations related to climate, commerce, energy, health care, and other realms. The demise of Chevron makes it easier for special interests to successfully challenge federal agencies in court—and to tie up pending regulations with nuisance lawsuits.
Adding insult to injury was Corner Post Inc. v Board of Governors, in which the majority stunned observers by ruling that the six-year statute of limitations for challenging federal regulations begins not when a regulation is first enacted, but rather when the party who brought the complaint was first affected. Corner Post puts Loper on steroids, making almost any regulation fair game.
These decisions, Dale says, “emasculate” the rulemaking ability of highly technical federal agencies, “because they’re going to be worried—correctly—about the extent to which litigation will bring them to court, and maybe invalidate their regulations.”
Loper “unleashes so much chaos,” concurs Georgetown Law professor Brian Galle, who teaches courses in taxation, nonprofits, and behavioral law and economics. “I think you will see a massive wave of antiregulatory lawsuits.”
“A rule of judicial humility gives way to a rule of judicial hubris,” Justice Kagan wrote in her Loper dissent. “The majority disdains restraint, and grasps for power.”
Tribune Media Company barely let the ink dry on the Loper ruling before mounting a challenge to IRS guidelines designed to curb what it calls “abusive basis-shifting” by partnerships. Last Wednesday, a lawyer for the IRS commissioner wrote to a federal appeals court contesting the Tribune challenge and pointing out that the agency had not relied on Chevron in its determination.
The Tribune company, the letter said, tried “to abuse federal tax rules to avoid a prodigious tax bill when it sold the Chicago Cubs and related assets. That ran afoul of, among other things, the partnership anti-abuse rule, [which] is supported by a long and unbroken history of judicial doctrines and congressional enactments empowering the IRS to combat the kind of chicanery attempted here.”
The IRS seems to have a solid case here, but that’s not the point. The point is that the agency will be forced to divert more of its hard-won and embattled resources to fend off the coming firehose of legal actions. “There’s such a long list, especially when you start talking about small businesses,” Galle says. Major law firms, Dale points out, have been reaching out to clients and holding webinars on what these rulings might mean for them. (This one highlights various “opportunities” and “avenues for challenge.”)
Lawmakers, too, have taken a keen interest in weaponizing Loper. Also last Wednesday, House Republican committee chairs sent letters to a host of agencies and Cabinet heads—including Treasury Secretary Janet Yellen—asking them to describe how Chevron‘s demise will affect their rulemaking. “We’ve already seen how frequently federal agencies will abuse their authority,” House Majority Leader Steve Scalise (R-La.) said in the announcement. “We intend to ensure agencies are held accountable following the court’s ruling and observe the proper checks on their power.”
“The big picture to me is the court grabbing power,” says Steven Rosenthal, who drafted tax law for Congress as a former staff attorney for the bipartisan Joint Committee on Taxation. “If that goes unchecked, it vastly diminishes the ability of Congress to write statutes and the executive branch to administer them. Everything becomes an interpretive question to be resolved by the courts.”
Justice Elena Kagan had a similar reaction. The Loper majority “flips the script,” she wrote in her scathing dissent (see page 82). “A rule of judicial humility gives way to a rule of judicial hubris…The majority disdains restraint, and grasps for power.”
Tax is a peculiar beast. Lawmakers, recognizing that they often have no clue what they’re doing, give the IRS and Treasury Department an unusual degree of statutory authority to craft workable tax rules and “fill in the details,” as Chief Justice John Roberts wrote for the Loper majority. (See page 17.)
“When the best reading of a statute is that it delegates discretionary authority to an agency,” Roberts wrote, the court’s role is “to effectuate the will of Congress subject to constitutional limits.” These last four words, Rosenthal fears, may signal the court’s future willingness to rule that Congress is delegating more of its power to an agency than the Constitution allows.
Justice Kagan wrote in her Loper dissent that themajority, in killing Chevron, had revived a legal test from the 1944 case Skidmore v. Swift, which held that “agency interpretations ‘constitute a body of experience and informed judgment’ that may be ‘entitled to respect,’” she wrote, but, “If the majority thinks that the same judges who argue today about where ‘ambiguity’ resides [in statutory language] are not going to argue tomorrow about what ‘respect’ requires, I fear it will be gravely disappointed.”
Indeed, the issue for the IRS is that lawyers for corporations and ultrawealthy taxpayers are already starting to throw spaghetti at the wall to see what will stick.
Every time the IRS moves to close an abusive loophole, it is “interpreting the statute to say thatcan’t be what Congress meant,” Galle told me. Such interpretations, he says—which would include the aforementioned partnership guidelines and the IRS’s warnings about wealthy taxpayers claiming “inappropriately large deductions” for conservation easements—are now more vulnerable to legal challenges.
The justices “had the hubris to believe that they alone can solve problems. They interpret the Constitution in a way that that leaves our government in disrepair.”
Let’s not forget that the IRS has only just begun to recover from decades of Republican-imposed shortfalls, and is still a long way from being fully back on track. “It’s hard to even fathom how far behind their rulemaking is,” says Galle, who is interested in rules around charitable giving. The IRS, for example, has long been mulling rules for donor advised funds, “the new kind of pet charities of a certain group of rich people,” he says. The agency “was supposed to create those rules in 2009, and they haven’t even proposed some of them yet.”
Galle also foresees “upstream pressure” on “the drafters and the general counsel’s office” to make rules that are more resilient to litigation—“which the IRS is not staffed for: They have kind of had their hands over their eyes and their fingers in their ears to warnings that the anti-regulatory tide is eventually going to pull them out to sea.”
Rosenthal finds the notion of so much judicial intervention hard to stomach. If Congress doesn’t have the capacity to deal with the intricacies of tax, he says, “the courts are even worse positioned. Each justice has, like, three or four clerks who are three years out of law school. Congress at least has technical experts like myself—lawyers and economists and others.”
“The court doesn’t have any of those facilities,” Rosenthal continues. “They just had the hubris to believe that they alone can solve problems. They interpret the Constitution in a way that that leaves our government in disrepair, and I think that’s by design. I think that’s what they want.”
Dale predicts the rulings will result in a year or two of gridlock in the federal courts, at which point “Chief Justice Roberts is going to say, this is a terrible problem and in order to allow people to have their rights determined, we need more federal judges. And the Congress is going to say okay. And so we’re going to have an enlargement of the federal judiciary, all of whom serve for life terms.”
If that happens, Dale says, whomever happens to be president will have the opportunity to make lots and lots of appointments, and “we’ll see the policy impact for 40 or 50 years.”
Just when the IRS was starting to get its mojo back, the Supreme Court had to go and throw a wrench into the works.
By now, most civic-minded Americans will have heard about the recent high court rulings that threaten to crush the administrative state, crippling the government’s ability to enact and enforce critical regulations that advance the nation’s interests and protect her citizens.
My colleague Jackie Mogensen recently described how a 2023 Supreme Court decision limiting the EPA’s jurisdiction has made way for polluted rivers. June’s rulings bode far worse, for both the natural environment and efforts to combat climate change. Colleague Nina Martin has examined how the new rulings will be weaponized to gut reproductive rights. The New Republic’s Timothy Noah covered how they may affect the banking sector—and the economy. Others have looked at impacts on health care. And so I set out to determine the extent of the chaos the court’s rulings will unleash on the federal tax system.
Short answer: Nobody knows, but it won’t be pretty.
Loper “unleashes so much chaos,” says Georgetown Law professor Brian Galle. “I think you will see a massive wave of antiregulatory lawsuits.”
Tax law is extraordinarily complicated. So much so that few lawmakers have any hope of understanding its nuances. Attorneys who specialize in tax, as one of my sources points out, tend to go beyond law school to obtain a master’s degree. Tax is also a realm that demands long-term planning by individuals and businesses. Stability is important. But with the Supreme Court latest actions, “what used to be fairly settled law now becomes potentially unsettled,” says attorney Harvey Dale, who has taught tax at the New York University School of Law for more than four decades. “It’s a very, very bad outcome.”
Two rulings in particular “will bring much more litigation into the federal courts. I’m talking hundreds, maybe thousands of litigations trying to take down regulations, some of which may be 50 years old. So that unsettles planning for the entire nongovernmental sector,” Dale says.
First and most notable is Loper Bright Enterprises v. Raimondi, wherein the Supreme Court majority killed the so-called Chevron deference. Chevron is the legal standard that has long guided career experts at federal agencies as they carried out the intent of Congress, translating broad legislative strokes into enforceable regulations related to climate, commerce, energy, health care, and other realms. The demise of Chevron makes it easier for special interests to successfully challenge federal agencies in court—and to tie up pending regulations with nuisance lawsuits.
Adding insult to injury was Corner Post Inc. v Board of Governors, in which the majority stunned observers by ruling that the six-year statute of limitations for challenging federal regulations begins not when a regulation is first enacted, but rather when the party who brought the complaint was first affected. Corner Post puts Loper on steroids, making almost any regulation fair game.
These decisions, Dale says, “emasculate” the rulemaking ability of highly technical federal agencies, “because they’re going to be worried—correctly—about the extent to which litigation will bring them to court, and maybe invalidate their regulations.”
Loper “unleashes so much chaos,” concurs Georgetown Law professor Brian Galle, who teaches courses in taxation, nonprofits, and behavioral law and economics. “I think you will see a massive wave of antiregulatory lawsuits.”
“A rule of judicial humility gives way to a rule of judicial hubris,” Justice Kagan wrote in her Loper dissent. “The majority disdains restraint, and grasps for power.”
Tribune Media Company barely let the ink dry on the Loper ruling before mounting a challenge to IRS guidelines designed to curb what it calls “abusive basis-shifting” by partnerships. Last Wednesday, a lawyer for the IRS commissioner wrote to a federal appeals court contesting the Tribune challenge and pointing out that the agency had not relied on Chevron in its determination.
The Tribune company, the letter said, tried “to abuse federal tax rules to avoid a prodigious tax bill when it sold the Chicago Cubs and related assets. That ran afoul of, among other things, the partnership anti-abuse rule, [which] is supported by a long and unbroken history of judicial doctrines and congressional enactments empowering the IRS to combat the kind of chicanery attempted here.”
The IRS seems to have a solid case here, but that’s not the point. The point is that the agency will be forced to divert more of its hard-won and embattled resources to fend off the coming firehose of legal actions. “There’s such a long list, especially when you start talking about small businesses,” Galle says. Major law firms, Dale points out, have been reaching out to clients and holding webinars on what these rulings might mean for them. (This one highlights various “opportunities” and “avenues for challenge.”)
Lawmakers, too, have taken a keen interest in weaponizing Loper. Also last Wednesday, House Republican committee chairs sent letters to a host of agencies and Cabinet heads—including Treasury Secretary Janet Yellen—asking them to describe how Chevron‘s demise will affect their rulemaking. “We’ve already seen how frequently federal agencies will abuse their authority,” House Majority Leader Steve Scalise (R-La.) said in the announcement. “We intend to ensure agencies are held accountable following the court’s ruling and observe the proper checks on their power.”
“The big picture to me is the court grabbing power,” says Steven Rosenthal, who drafted tax law for Congress as a former staff attorney for the bipartisan Joint Committee on Taxation. “If that goes unchecked, it vastly diminishes the ability of Congress to write statutes and the executive branch to administer them. Everything becomes an interpretive question to be resolved by the courts.”
Justice Elena Kagan had a similar reaction. The Loper majority “flips the script,” she wrote in her scathing dissent (see page 82). “A rule of judicial humility gives way to a rule of judicial hubris…The majority disdains restraint, and grasps for power.”
Tax is a peculiar beast. Lawmakers, recognizing that they often have no clue what they’re doing, give the IRS and Treasury Department an unusual degree of statutory authority to craft workable tax rules and “fill in the details,” as Chief Justice John Roberts wrote for the Loper majority. (See page 17.)
“When the best reading of a statute is that it delegates discretionary authority to an agency,” Roberts wrote, the court’s role is “to effectuate the will of Congress subject to constitutional limits.” These last four words, Rosenthal fears, may signal the court’s future willingness to rule that Congress is delegating more of its power to an agency than the Constitution allows.
Justice Kagan wrote in her Loper dissent that themajority, in killing Chevron, had revived a legal test from the 1944 case Skidmore v. Swift, which held that “agency interpretations ‘constitute a body of experience and informed judgment’ that may be ‘entitled to respect,’” she wrote, but, “If the majority thinks that the same judges who argue today about where ‘ambiguity’ resides [in statutory language] are not going to argue tomorrow about what ‘respect’ requires, I fear it will be gravely disappointed.”
Indeed, the issue for the IRS is that lawyers for corporations and ultrawealthy taxpayers are already starting to throw spaghetti at the wall to see what will stick.
Every time the IRS moves to close an abusive loophole, it is “interpreting the statute to say thatcan’t be what Congress meant,” Galle told me. Such interpretations, he says—which would include the aforementioned partnership guidelines and the IRS’s warnings about wealthy taxpayers claiming “inappropriately large deductions” for conservation easements—are now more vulnerable to legal challenges.
The justices “had the hubris to believe that they alone can solve problems. They interpret the Constitution in a way that that leaves our government in disrepair.”
Let’s not forget that the IRS has only just begun to recover from decades of Republican-imposed shortfalls, and is still a long way from being fully back on track. “It’s hard to even fathom how far behind their rulemaking is,” says Galle, who is interested in rules around charitable giving. The IRS, for example, has long been mulling rules for donor advised funds, “the new kind of pet charities of a certain group of rich people,” he says. The agency “was supposed to create those rules in 2009, and they haven’t even proposed some of them yet.”
Galle also foresees “upstream pressure” on “the drafters and the general counsel’s office” to make rules that are more resilient to litigation—“which the IRS is not staffed for: They have kind of had their hands over their eyes and their fingers in their ears to warnings that the anti-regulatory tide is eventually going to pull them out to sea.”
Rosenthal finds the notion of so much judicial intervention hard to stomach. If Congress doesn’t have the capacity to deal with the intricacies of tax, he says, “the courts are even worse positioned. Each justice has, like, three or four clerks who are three years out of law school. Congress at least has technical experts like myself—lawyers and economists and others.”
“The court doesn’t have any of those facilities,” Rosenthal continues. “They just had the hubris to believe that they alone can solve problems. They interpret the Constitution in a way that that leaves our government in disrepair, and I think that’s by design. I think that’s what they want.”
Dale predicts the rulings will result in a year or two of gridlock in the federal courts, at which point “Chief Justice Roberts is going to say, this is a terrible problem and in order to allow people to have their rights determined, we need more federal judges. And the Congress is going to say okay. And so we’re going to have an enlargement of the federal judiciary, all of whom serve for life terms.”
If that happens, Dale says, whomever happens to be president will have the opportunity to make lots and lots of appointments, and “we’ll see the policy impact for 40 or 50 years.”
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